Journal
MOLECULES
Volume 27, Issue 14, Pages -Publisher
MDPI
DOI: 10.3390/molecules27144549
Keywords
ferrocifen; hydroxylactam; N-acyliminium ion; anticancer activity; ferrocene
Funding
- National Agency of Research (ANR), NaTeMOc project [ANR-19-CE18-0022]
- Feroscan
- France Relance programme [P21/1165]
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The addition of imide entities to the ferrociphenol scaffold enhanced cytotoxic activity. By converting alpha-hydroxylactams to N-acyliminium ions, various substituents were grafted to the imide motif, resulting in diverse cytotoxic activities on breast cancer cell lines.
The [ferrocene-ene-phenol] motif has been identified as the pharmacophore responsible for the anticancer activity of the family of ferrocene-based molecules coined ferrocifens, owing to its unique redox properties. The addition of imide entities to the historical ferrociphenol scaffold tremendously enhanced the cytotoxic activity of a large panel of cancer cell cultures and preliminary studies showed that the reduction of one of the carbonyl groups of the imide groups to the corresponding alpha-hydroxylactams only slightly affected the antiproliferative activity. As a continuation to these studies, we took advantage of the facile conversion of alpha-hydroxylactams to highly electrophilic N-acyliminium ions to graft various substituents to the imide motif of phthalimido ferrocidiphenol. Cell viability studies showed that the newly synthesized compounds showed diverse cytotoxic activities on two breast cancer cell lines, while only one compound was significantly less active on the non-tumorigenic cell line hTERT-RPE1.
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